HuagongsheHuagongshe Chemistry Print Report · For research reference only
(2-Ethoxy-5-oxo-tetrahydrofuran-3-yl)-carbamic acid allyl ester → 1-[2-(4-Amino-3,5-dichloro-benzoylamino)-propionyl]-pyrrolidine-2-carboxylic acid (2-ethoxy-5-oxo-tetrahydro-furan-3-yl)-amide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | (2-Ethoxy-5-oxo-tetrahydrofuran-3-yl)-carbamic acid allyl ester | HCID 22149038 | — |
| Reactant | 1-[2-(4-Amino-3-chloro-benzoylamino)-propionyl]-pyrrolidine-2-carboxylic acid (5-oxo-2-phenethyloxy-tetrahydro-furan-3-yl)-amide | HCID 22977512 | — |
| Reactant | 1-[2-(4-Amino-3,5-dichloro-benzoylamino)-propionyl]-pyrrolidine-2-carboxylic acid tert-butyl ester | HCID 68950984 | — |
| Product | 1-[2-(4-Amino-3,5-dichloro-benzoylamino)-propionyl]-pyrrolidine-2-carboxylic acid (2-ethoxy-5-oxo-tetrahydro-furan-3-yl)-amide | HCID 22977491 | 54% |
Reaction Steps
Prepared from (2-ethoxy-5-oxo-tetrahydro-furan-3-yl)-carbamic acid allyl ester and 1-[2-(4-amino-3,5-dichloro-benzoylamino)-propionyl]-pyrrolidine-2-carboxylic acid tert-butyl ester according to the method used for 98a to afford 158 mg of title compound (54% yield). 1H-NMR (500 MHz, 1:1 CDCl3:CD3OD) δ 1.08-1.30 (m, 3H), 1.32-1.52 (m, 3H), 1.72-2.44 (m, 4H), 2.40-3.05 (m, 2H), 3.50-3.97 (m, 4H), 4.25-4.70 (m, 3H), 4.70-4.86 (m, 1H), 5.33 (s, 0.4H), 5.47 (s, 0.1H), 5.56 (d, 0.4H), 5.62 (d, 0.1H), 7.50 (s, 1H), 7.80 (s, 1H). Analytical HPLC: 10.84 min. LC-MS (ES+): m/e=501.2 (M+H+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07358273B2 |
| Source dataset | uspto-grants-2008_04 |
| ORD ID | ord-d6c8c44ff78a4fc499be25aafa89b819 |
| Source note | uspto-grants-2008_04 |